Pretend Prostitute for a Night

[Mr Stag]

At the time, I was 38 and single, and a business convention that I liked to attend was going to be held in my city, which disappointed me greatly. I prefer visiting a new city, and driving to a local event is a pain, as I would have to drive home each night; and, once my associates knew I had a car, they would be asking to be driven to their hotels or restaurants. So, I decided not to attend that year—then at the last minute, I changed my mind. I had a plan. I would take a taxi to the hotel and act as if I had flown in. One problem: I couldn’t get a hotel room. I called around and it was the same, no available rooms. Just as I was about to give up, I got a call back from the hotel where the convention was being held, explaining that they had a cancellation, but it was for a shared room, so I would have a male roommate. I took it and called for a cab. I also left a message with my girlfriend, a 29 year-old 3rd-grade teacher, telling her where I was going.

Everything was going well at the convention and my girlfriend called me, asking me if she should drive into town to have dinner with me. I didn’t have any plans yet, so I told her to come. My guess was that she was fearful that I would pick up some woman and spend the night with her, as my girlfriend showed up dressed to kill: heels, short leather skirt, expensive nylons, lacy top and expensive jacket. We had a great meal and, before she drove back to her place, she wanted to head back to my room for some quick sex. I explained that I had a roommate and that we might not have the chance.

Sure enough, he was in the room when we arrived. He eyed my girlfriend up and down, as we walked in. I asked him if he could leave for an hour. He acquiesced and left. Within five minutes, we were naked and fucking as if our lives depended on it. As she put her clothes back on, I held her bra in my hand, as I asked her not to wear it. She thought that I was being silly, but she nonetheless put her bra in her purse and slipped on her black, semi-see-through top and her jacket. With the jacket’s buttons fastened, she still looked modest, but with her jacket open, she was sexily indecent. It was right then that I had an idea.

I quit getting dressed and began kissing her in earnest. I wanted to stall, so my roommate might see her braless before she left. We were so worked up that we fucked again. Well, he gave me an hour and fifteen minutes before knocking on the door. I let him in and my girlfriend was in the bathroom. She came out with her bra still in her purse and her jacket unbuttoned as I had requested. She said hello to my roommate, gave me a quick kiss, and headed towards the door. As she stepped out, she said to me, “Call me, if you would like to do that again.” I am sure that my roommate heard her.

My roommate was impressed and he asked me if I had just picked her up. I was about to say that she was no lady, she was my girlfriend, but instead I told him that she was a prostitute. His eyes went big. Instantly, I felt bad for having made that lie, so I lied again, telling him that she was actually a high-school teacher, which was half-true as she was teacher, and that she was married to a man who liked her to pretend that she was a whore, which was 100% a lie. I told him that I knew her husband well and that I made all the arrangements with him.

My stunned roommate wanted to know how much she cost. My answer was nothing, as I paid her with $300 worth of kid’s play money. He then wanted to know why the husband allowed her to be fucked by other men. I gave him an explanation of how some men enjoyed sharing their wives, which was extremely easy for me to do as I had shared my ex-wife many times, so I knew exactly how such a husband would feel, as I had been one myself. Later that night, he asked if he could become her client for an hour. I told him that I would ask her husband.

The next day was Saturday and my girlfriend drove out to meet me for lunch. She showed up in her jeans and a sweater. I told her about my conversation with my roommate and she was both upset and tickled by it. At first, she was dismayed that my roommate believed that she was a prostitute, even a fake prostitute, and she was a bit miffed that wanted her services. I took the edge off it by telling her that I was sure he believed the story because he couldn't imagine me having such a stunningly sexy girlfriend. The more we talked about it, the less upset and the more amused and delighted she became at the thought of playing the whore. Somehow the background story of her being married to a man that enjoyed sharing her body and the play money took the ugly edge off of "selling" her body. It didn't hurt that I revealed how attractive my roommate thought she was.

After our long lunch, she asked me if she should show up again that night for dinner and sex. I actually had hoped that she wouldn’t ask, as I planned on getting together with some business contacts that night, which my business could use. But this odd situation of my roommate believing that she was a whore, albeit a make-believe whore, and her fantasizing about being a whore, had me wondering just what she would wear and how she would behave around my roommate. So, I told her yes and to dress up for it.

She showed up early, crazy early, wearing a miniskirt, an attractive blouse, and brown leather boots. She looked sexy in her outfit, but I don’t think that she looked anything like a prostitute. A sexy school teacher, yes; a prostitute, no. My guess was that she wanted to erase the whore image from my roommate’s mind, but I was wrong, totally wrong. She opened her purse and showed me that she had brought some toy money, $300 worth. I asked where she got it, and I was told that all good 3rd grade teachers must own many crazy things. I just stared at the tiny fake bills, not knowing what she had in mind, because it just seemed unthinkable that she would be thinking what I was thinking. She asked if that was enough money for my roommate to buy her services that night. All that I could get out of mouth was, “You mean you want him to,” before I could say anymore, she interrupted me and told me that she did.

The problem was that I hadn’t seen my roommate since that morning, so I didn’t get a chance to book an exclusive hour of the room from him or tell him that he could buy her instead of me or with me. We talked out a strategy. We soon had a plan. She didn’t want to be alone with him, so I would call my own phone at home and pretend to be talking to her imaginary husband, who would tell me that my roommate could buy her services only if I also participated, as he didn’t know the fellow. It was a good plan I thought, but it held at least one problem: my roommate may not want to be in a threesome. Her answer was that I didn’t have to participate, as I could just stay in the room with them, keeping an eye on her. I was both a tad upset to be left out of the action and quite a bit turned on by the thought of playing the voyeur.

We went out for a quick dinner and I bought two condoms from the machine in the restroom. We returned to my room for a quick blow job. I loved it, but we were getting worried that my roommate wouldn’t show up. I decided that we should do a dry run of her encounter with him, so we role played several variations and I practiced my fake phone conversation. I was getting horny again and I was tempted to just go ahead and fuck her, when we heard the knock on the door. He had arrived.

I did most of the talking. He was all nerves, his eyes furtively scanning my girlfriend's body, but eager to play the John. I made my fake phone call and pretended to listen carefully, as my answering machine message poured into my ear. I hung up and explained the deal to him: that she could service him, but I would have to remain in the room and he would have to wear a condom, as her husband didn’t know him. He quickly agreed and she nodded her approval. I took him aside and handed him one condom and all the play money to give her. I sat in the only chair in the room and watched.

The negotiation portion went smoothly, with him handing her the fistful of play money for one hour of sexual bliss. She tucked the fake money in her purse and began stripping in front of him. She followed my advice of going slowly and keeping her bra on until the very end. So, when she stood completely naked, save for her bra and boots, his eyes were bulging with anticipation as she unhooked her bra and pulled the cups off her breasts. Such lovely breasts she had, medium sized with light-brown nipples that rode high on her breasts. She asked him if he liked what he was seeing and he just nodded yes. She asked him to remove her boots, while she sat on his bed. She then beckoned him to stand, and she began to remove his shirt, then his shoes and socks, then his T-shirt and, finally, his shorts.

I was sitting behind him, so I couldn’t see his cock, but she told me afterwards that it was hard and quite suckable. She had him sit on the bed and she got on her knees in between his legs and licked his cock. He loved all the attention his cock was receiving and he let out many soft moans. Then he lay back on the bed and I saw his cock. It wasn’t huge or small, just a very serviceable six-incher.

He looked like he was going to shoot his load, so she released his cock from her mouth and she climbed onto the bed with him. I thought for sure that she would mount and ride him, but she placed her breasts in his face and rubbed her nipples against his mouth, while he lay as still as a cadaver. I told him that he was allowed to touch her for God’s sake and that seemed to free him from his self-imposed rectitude.

Fifteen minutes later, he collapsed on top of her, panting and sweating. It had been a good show, although brief. I figured that he was done for the night, but I was wrong. He brought his mouth down to her pussy and began eating her skillfully. I was impressed, as he soon had her squirming and writhing. Before she had a chance to orgasm, he was on top of her again, fucking with the same used condom. I had another condom in my jacket, and I was going to get it when he climbed off her and resumed his pussy licking. This went on for at least three times before he asked me if I had another condom. I gave it to him and he pulled off the used one.

As he opened the wrapper, she sucked his cock clean, a sex trick that I had taught her, as I love having my cock licked clean after fucking. Soon he was suited up and in her again. I knew that he wanted her to cum from his fucking her, but her toes tightly clenched up only while he was eating her. I doubt that real prostitutes ever cum, but he enjoyed trying to make it happen. I thought he would begin fucking her again, but he brought his condom-covered cock up to her mouth and she eagerly sucked him. After a few minutes, she asked him if he wanted to fuck her doggy style; he did.

I loved it, as I could finally see everything: her breasts sway back and forth, her ass bounce and jiggle with each of his thrusts, his face contort, and her gasps. I wish that I had a movie camera—or any camera. For a short, balding guy in his early 30s, he really gave her a serious pounding. Just when I thought he was about to explode, he pulled out and fell on his back, his cock pointing to the ceiling—he was too winded to continue. She climbed atop him and began fucking him in earnest. She then called me over to hold her hands, so she could ride him better. It was an amazing sight, her tits swinging wildly, her ass flying up and down on him, his face contorted into a grimace of pleasure. I was more than just holding her steady, I was helping pull her up and down on his cock. He came and she kept fucking him until she couldn't continue and collapsed on his chest.

I had only bought two condoms, so I figured that this was the end, but both of them wanted to get their full hour. They kissed and rolled about and I was impressed to see his cock still hard. She had also noted his stiffy and she unrolled his used condom and began sucking his cock clean. Soon, they were in the 69 position, with her on top. He kept eating her until she came, a wonderfully violent orgasm, her legs quaking, her mouth open in a silent scream of pleasure. She tried to suck his cock, but it had gone soft.

One hour, five minutes. I had to fuck her, so I pulled off my clothes and climbed on the bed with them. She instantly opened her legs for me and I fucked her bareback with him lying just a few inches away from us. Instantly, my naked cock could feel ho w different her vagina felt, looser, warmer, wetter. She was as wet as if he had dumped two loads in her.

I asked her if she would be telling her husband all the details about how two strange men had just fucked her. She told me that I wasn’t a stranger, which upset me, as I didn’t want her to blow our story. After telling her that I wasn't a stranger only because her HUSBAND let me fuck her so often but that my roommate was certainly a stranger. She played along told us how much her husband liked to have other men fuck her, while I was slowly fucking her and he was playing with her nipples.

I said something along the lines of, did her husband like it because he had a little dick? Her answer was awesome; she said that his cock was much, much larger than ours, both much longer and much thicker; and that he merely liked hearing all the sexy details when she got home. Then she said that if prostitution were legal, she would certainly be a real one, so she was super lucky that her husband allowed her to play one occasionally. I asked if her husband would like her to be a real prostitute and she told us that nothing would make him happier, spending his day thinking about how she had been naked under a strange man, having her come home after a hard day fucking, listening to her detail all that she had experienced at work.

After I came, she got up, dressed, and left. While I was getting dressed, my roommate who was still naked and semi-erect said, “I sure wish I could convince my wife to pretend to be a whore—at least once.”

I didn't know that he was married. I asked why he wasn’t wearing a wedding ring. He admitted to wanting to score at the convention. I told him that he was a fool, as it much easier to pick up a woman with the ring on (which is true, as the ring implies that you are a safer choice, that you are worthy of a wife, that you will not stalk her or pester her afterwards, that you probably know how to eat pussy and how to fuck).

When I exited our room, my girlfriend ran up to me and gave me a huge, wet kiss, which smelled of cock. As we rushed down the hall, she thanked me for the fantastic experience. We went out for a drink and then I fingered her to quaking orgasm in her car before she drove home.

[Triceratops]

She is a keeper

[Nothing2see]

Amazing story! Thank you.

[Luv2watchher]

It sounds like everyone involved enjoyed the experience. A great way to liven up a conference (I have always found them a little dull). Thanks for telling us all about it.

[sdbuffalo]

Wonderful story!
Have you made any plans (or opportunities) to do it again?
If it should happen, please report it here.
Great story, thank you.

[BigCharlie]

Great story, you are very luck to have such a hot girlfriend.